A few days later, Amber gets back to Matt’s place. It is a little on the late side, as she comes directly from her evening class. She has not seen Matt since her birthday dinner and sleep over. She is anxious to get another look at her bag of sex items. They had tried the massage oil and the flavored lube, but she wants to check out the toys more.
Matt gets them an after dinner liquor and grabs the velvet bag with the lotions and toys. First, he pulls out the double dildo. “This is a toy for you and Kelly. There’s an end for each of you.”
Amber examines it. “It looks interesting. Are there any instructions?”
“I’m sure Kelly will know what to do with it.” Matt is not an expert either, having only seen one in operation in a porn video.
Amber picks up the butt plug. “I’m not sure I’m going to like this thing.” The butt plug is only about four inches long. It is less than an inch across at the widest place. It has a wide flange on the bottom to keep it from going up the ass too far.
Matt reassures her, “The butt plug can be fun if we are gentle back there. Let me show you, Amber?”
Matt and Amber get a refill on their after dinner drink and head to Matt’s bedroom. Matt had the room all set for them to play. The lights are dim and a couple candles are flickering. There is a towel on the bed. The bottles of lube and lotion are on the nightstand. Matt has an extension cord ready for her vibrator. He puts the butt plug on the nightstand; Amber gets her vibrator ready. They slowly undressed each other, only pausing occasionally to kiss.
Amber gets on the bed on her tummy. Matt begins massaging her back with lotion. He has learned this is a sure fire way to get laid with Amber. Rub her back with lotion, and it is only a matter of time before she spreads her legs for cock. She moans softly, as he massages her back and ass for several minutes. Matt asks her to get up on all four. In this position, Amber can look between her legs and see her reflection in the mirror closet doors facing Matt’s bed. She can watch Matt working on her ass and back. Matt loves this position; it spread her ass cheeks to reveal her pussy and asshole…his favorite view.
He massages her back and ass a little more in this position. He soon switches to lube and begins massaging her pussy. He makes sure he is off to the side, so she can watch her pussy massage in the mirror. After several minutes massaging her pussy, he begins including her asshole in the massage with his other hand. Matt puts plenty of lube on her butt hole, so the butt plug will enter her easily. Massage time is almost over. Matt lubes up his cock to fuck her.
Matt puts his cock in her pussy and fucks her doggy style. Only a little at first, not getting deep. He grabs the small butt plug and puts lots of lube on it. He keeps the head of his cock in her pussy, but withdraws enough to slide the butt plug tip into her asshole. He does not want to put the butt plug in all the way.
His plan is to move the plug back and forth in her ass, as he fucks her pussy with his cock. The wide base of the butt plug is against his abdomen just above his cock. He is now in position. He pushes his cock into her pussy; the butt plug moves into her ass. He fucks her slowly. She gets both his cock and the butt plug, going in and out of her at the same time. She moans and grabs her vibrator for her clit. She is in sexual Never, Never Land.
Matt can watch the butt plug going in and out of her ass, as he fucks her. He is careful not to push it in too deep. It is extremely exciting, watching her taking the plug in her ass; Matt has to be careful not to come too quickly.
She is close to orgasm. Matt keeps the fucking of both holes going…she moans loudly. He gives her all of his cock; the butt plug is deep in her ass as she comes. Watching the butt plug the entire time, has made Matt’s cock rock hard. As she orgasms, he does not have to wait any longer. He fucks her pussy with long strokes, while the butt plug continues to stroke her ass. His cock stiffens and pulsates. He fills her pussy with cum. The constant simulation to her pussy, after her orgasm, is causing her to moan the entire time. He has kept her pussy in a prolonged state of ecstasy.
Matt would have loved Amber to spend the night again, but he has to go to work in the morning. He walks her to the car, hugs her, and kisses her. He tells her to drive safely on her way home. One last hug and she is gone.
***
Kelly has continued to look for guys or girls online. This is either dating sites or those that contain ads from potential playmates. She rarely finds anyone worthwhile but even reading the ads is fun.
She always corresponds online with prospective guys to check them out and try to make sure they are not goofy. There are plenty of goofy ones, which is not always easy to figure out. One guy said he was big. Kelly made the mistake of thinking he was hung. Turned out he was 400 pounds big. She never got around to finding out his cock size.
Another guy was a clean freak and asked if she minded cleaning her pussy right before sex. He volunteered to bring the baby wipes.
Then one day, while checking out ads online, Kelly comes across a guy that wants to be butt fucked by a woman with a strap-on. He calls it pegging. Kelly has not heard that term before. She has seen the strap-on toys at the adult store but figured they are used for one girl to fuck another. Kelly had never used one, but they certainly looked interesting. It has never occurred to her that a girl would actually fuck a guy in the ass with one. There were a few stories in her sexy magazines about such actions, but she thought it was probably made up…to be a good story.
The ad got Kelly’s interest up a little, and she answered the guy. They exchanged a few emails. The guy seems normal and is able to write…spelling most of the words correctly. His name is Doug. He told her it is exciting for him to be on all four with his naked ass up and a girl behind him. The girl looking at his asshole, lubing it, and then fucking him is a huge turn on.
Next, Kelly wants to talk to him on the phone. She figures she might be able to tell more about him by listening to his voice, rather than just an email. The phone call contact with Doug goes great. He sounds like a real person. He does not get nasty on the phone, but matter of fact on what he would like. Kelly thinks she would like it too, and they make a coffee date for the next afternoon.
At the coffee shop, Doug is extremely nervous. He probably would have been more relaxed if Kelly was not so attractive. The thought of her working on his ass and fucking him, is so erotic, he is trembling. As much as Doug tries to act normal, he cannot be himself.
“Kelly, I’m sorry, but you are such a nice looking and pleasant woman, and I’m so nervous; I don’t think I’m coming across very well.”
“You’re doing Ok.”
“Thanks, I’m normally very comfortable in these kinds of situations, but with you and the thought of what we are talking about doing, has my brain all fogged up in anticipation.”
“You! What about me? I have to worry I’m not going to hurt you back there, make sure I lube your hole enough, not stretch you too much, and only bury the strap-on dildo to its balls now and then.” She gives him a little smile. He does not say anything for a while. Kelly is not sure he did not have a pre-mature orgasm in his underwear.
Kelly asks him if he has a strap-on. He admits he did buy one in the anticipation of finding the right girl. She likes him. It is certainly a little on the unusual side, but he seems like a nice normal guy…that just would like to be fucked in the ass by a woman. It sounds reasonable to her.
They make a date for the following week. They will play at his house, which makes it a little more nervous for her. If he did not seem like a regular person, she would probably have gotten someone to come with her. Kelly is comfortable with him and is turned on about fucking him with his strap-on.
Kelly arrives right on time. Doug has set up a place for then on the living room floor with a big quilt laid out. He has lube bottles nearby and several towels. Kelly sees the strap-on sitting on the coffee table. It is all new to her, and she feels the excitement. Doug has on a pair of jeans and a tank top. He is not dressed up at all. He offers her a drink; she settles for a diet cola. There is only a brief period of uncomfortableness.
They talk for a few minutes. Kelly asks, “Show me your strap-on.” He gets it off the table and hands it to her. She is actually trembling a little, thinking she is going to be wearing this thing, and sliding it up Doug’s ass. She is hot to do it. “I’m ready to give this thing a try. Are you ready to receive?”
Doug does not answer her, but instead begins removing his clothes. Kelly also starts getting naked. It is not an erotic undressing; more like getting nude is just a step they had to go through. Doug has a very nice muscular body. He is probably late thirties or early forties. He is a little taller than she is. His flat tummy and nice ass are a big turn on for her.
She picks up the strap-on. The cock part is about seven inches long and more than an inch in diameter. It is a little pointed on the end, which should make it easier to get in. Doug offers to help her put it on. He adjusts the straps until it is snug. Her cock, as well as his, is pointed above the horizontal.
“You ready Doug?” She asks, as he assumes the position on the quilt. He is on his knees and forearms; his ass is up. He has very muscular legs, and his ass is perfect. She loves the view from behind him. Doug’s asshole is clearly visible. His balls are hanging between his legs. She cannot see his cock in this position; it is hard and pointed at his head. Kelly is ready to fuck him.
She grabs the bottle of lube and puts a coating on her dick. Then she squirts lube down the crack of his ass, letting it drip over his hole. Kelly massages the lube into his asshole with her fingers and runs a finger into his butt. She figures she is going to need a lot of lube back there. Kelly adds lube a couple times, making sure she gets plenty into the opening. Doug is quivering, as she works his butt hole. He is so ready to be butt fucked.
Kelly puts one more coating of lube on her cock and moves between his cheeks. In this position on his knees, his butt crack is spread apart. She grabs one of his butt cheeks with her left hand and guides her cock with her right hand. The pointed end of her dildo is right at the opening.
“Are you ready for my cock?” she asks.
***